Stereoselectivity at benzylic carbon

Autor: K. Ramdas, S.S. Mohorkar, K.G. Marathe, C.B. Singh, A. Hirwe
Rok vydání: 1986
Předmět:
Zdroj: Tetrahedron. 42:1539-1546
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(01)87374-9
Popis: Some reactions of 4-substituted flavans have been studied. 4-Chloro/bromo derivatives react under neutral conditions with phthalimide and acetonitrile leading to displacement or axial halogen by nitrogen with inversion. In contrast, irrespective of the stereochemistry, 4-hydroxy-derivatives react under acidic or basic conditions leading to axial attack by the nudeophiles SOCl2, PCl3, PCl5, SOBr2, PBr3, PBr5, acetonitrile and water, evidently through the intermediate formation of a benzylic carbocation.
Databáze: OpenAIRE